Chemistry Aldehydes & Ketones MDCAT 2017
PMDC Verified Question 66 of 94
The reaction of aldehydes and ketones with ammonia derivative \( G-NH_2 \) to form compounds containing the group \( >C=N-G \) and water is known as:
A
Nucleophilic addition
B
Electrophilic addition
C
Nucleophilic substitution
D
Addition Elimination
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Propolis Cognitive Error Autopsy

Official Correct Choice:
Option D: Addition Elimination
Concept:

The reaction between a carbonyl compound and a primary amine derivative (like hydroxylamine, hydrazine, etc.) proceeds via a two-step mechanism.

Formula:

$$ >C=O + H_2N-G \rightleftharpoons >C(OH)(NH-G) \longrightarrow >C=N-G + H_2O $$

Solution:

  • Step 1 (Addition): The nucleophilic nitrogen atom attacks the electrophilic carbonyl carbon, forming a tetrahedral carbinolamine intermediate.


  • Step 2 (Elimination): The intermediate is unstable and rapidly eliminates a molecule of water to form a stable carbon-nitrogen double bond.


  • Because the process requires both of these steps, it is formally classified as an Addition-Elimination reaction.


Why other options are incorrect:

Nucleophilic addition is only half the story; it ignores the water elimination. Electrophilic addition occurs in alkenes. Nucleophilic substitution typically involves replacing a leaving group attached to an \( sp^3 \) hybridized carbon, which is not the case here.

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